


Widomauk Kinktober 2018

by keefling



Category: Critical Role (Web Series)
Genre: Boot Worship, Breast Worship, Desperation, Edgeplay, Established Relationship, Formalwear, Hand Jobs, Kinktober 2018, Nipple Play, Nonbinary Character, Orgasm Delay/Denial, Other, Scent Kink, Semi-Public Sex, Sensation Play, Temperature Play, Trans Male Character, Wall Sex, Watersports, Xenophilia, distracted sex
Language: English
Status: Completed
Published: 2018-10-01
Updated: 2018-10-25
Packaged: 2019-07-20 12:57:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 8,388
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16137722
Author URL: https://archiveofourown.org/users/keefling/pseuds/keefling
Summary: A series of one-shots for Kinktboer 2018.





	1. Temperature Play

**Author's Note:**

> Kinktober is upon us! I have only picked out 12 prompts to give myself some breathing room. None of the chapters are related, unless otherwise specified. 
> 
> Update: 11/1: This challenge is finished. I was unable to write all 12 prompts in time, but please enjoy the 7 I have!
> 
> The master list of prompts came from [here,](https://kinktober2018.tumblr.com/post/171107184776/kinktober-2018) but I have switched them around and added some of my own. 
> 
> Note: Caleb is a trans man and Molly is nonbinary in all of these stories. I use gender-coded language to describe their genitals.

Pity is for people who fall down the stairs, while shame is reserved for those who fall up them.  The first step was hidden under the snow when it caught the toe of Caleb’s boot.  He fell with one arm out in front of him, hissing as his wrist bent back at a gruesome angle.  Relieved that no one was around, he picked himself up, brushed the snow from his knees and joined his friends in the tavern.  Caleb favored his left hand all evening, hoping that he was dextrous enough to avoid detection.

“Come to bed,” Molly said once they were settled in their room.  Exhausted from the journey, Caleb was more than happy to join them.  He kneeled on the bed, cupped Molly’s jaw in his hands and kissed them, breathing in Molly’s exhale and swallowing the soft groan that passed between their lips.  Molly responded with a happy whine, but when they covered Caleb’s hands with their own, Caleb pulled away and flinched.

“Are you hurt, dear?” Molly asked.

“It is just a bit sore,” Caleb insisted, cradling his swollen wrist in his opposite palm.  “I….I fell, but I am sure that it will be fine in the morning.”

“At least let me take a look at it,” Molly said.  Caleb reluctantly held out his hand.  He hissed when Molly gently bent his wrist back and forth.

“Looks like a sprain,” Molly said, gently rubbing their thumb over the swollen spot between the bones.  “Will you let me try something?”

“What is it?” Caleb asked.

“Just a bit of ice,” Molly said.  “Trust me?”

Caleb nodded, uncertain but curious.  Molly scratched their claws across the back of their neck and Caleb watched ice form on Molly’s bloody fingertips.  It might have shocked Caleb if he was not so used to seeing Molly make themself bleed during battle.

“Here, lie down and give me your hand,” Molly said, patting the mattress beside them.  “This’ll help the swelling go down.”

Caleb did as Molly instructed, resting his head on the pillow and his hand palm-up on Molly’s knee.  He sucked in a breath when Molly pressed their frost-covered fingers to Caleb’s wrist.

“How’s that?” Molly asked.

“Cold, but not unbearable,” Caleb answered truthfully.  It actually felt nice once he adjusted to the shocking change in temperature.  The painful throbbing eventually gave way to numbness, and he groaned his appreciation.

“It’s a shame you won’t be able to pleasure yourself for a few days,” Molly teased, sounding awfully chipper about it.

“I can use my other hand for that,” Caleb said, rolling his eyes.

“Oh?” Molly pinned Caleb’s other hand to the pillow beside Caleb’s head.  “Can you?”

“If you are going to be a brat, then no, I suppose I cannot,” Caleb huffed and furrowed his brow.

“I’m not cruel, darling,” Molly chuckled.  “I will take care of you until you’re better.”  They leaned in close, speaking softly against Caleb’s lips.  “Will you let me, sweetheart?”

“Mm, _ja,_ okay,” Caleb answered softly.  His reluctance melted away under Molly’s sly smile and half-lidded gaze.

“You seem to like it when I do this,” Molly said.  They dragged one nail down the side of Caleb’s neck, making the him gasp and shiver.  “Or am I wrong?”

“N-no, you are—I mean, _ja,_ yes, I do, I like that,” Caleb stuttered.  The melting ice dripped down his neck and pooled in the divot of his collarbone.

“Close your eyes, Caleb.  And please, let me know if it gets to be too much, alright?”

“Mmm, _ja,_ I will.”  Caleb obediently closed his eyes.  He felt Molly shift on the bed.  Not knowing when and where Molly would touch him next made Caleb’s heart beat faster in excitement.

Caleb gasped when he felt Molly trail their icy fingers over his ribs and down both sides of his sensitive stomach.  He heard Molly chuckling above him as he arched his back and scrunched up his face, trying not to make a sound.  He sucked in his gut, arched his back and squirmed helplessly from side to side.

Then, mercifully, Molly took their hands away.  Caleb shivered as the ice melted and dripped down his sides.

“Oh, _scheisse,_ ” he whined, gripping the sheets.  “It—it’s cold.”

“It’s ice, sweetheart,” chirped Molly.  “Of course it’s cold.”

Caleb wished he could glare at Molly, but he kept his eyes closed as he had been instructed.  He steeled himself for the next touch and wondered where it would be.  There was only so much lower Molly could go before they reached—

Caleb felt warm air waft over his thighs, followed by the lick of a hot tongue up the center of his pussy.

“Molly, _please,_ ” Caleb breathed, arching up into the heat before it disappeared.  

“Patience, love,” Molly said.  They shifted again, seating themself between Caleb’s knees.  They spread his legs apart and made a delighted sound in the back of their throat.  “You’re soaking wet,” Molly observed out loud, voice thick with arousal. “Did I do this to you?”

“Can’t help it,” Caleb muttered.  He turned his head to hide one side of his face in the pillow.  He felt so vulnerable, spread out before Molly, unable to close his legs as precum dripped from his slit, down his taint and onto the bed.

“I promised I would take care of you,” Molly purred.  They carefully parted Caleb’s lips with their thumbs and poked their tongue inside.  The split prongs of Molly’s tongue had frosted over.  The frigid muscle pushed inside of him, twisting and curling and setting Caleb’s nerves alight.

“ _Scheisse!”_ Caleb hissed in surprise, trying to squeeze his legs shut but finding Molly’s shoulders wedged between them.  He bucked his hips and trembled with the effort to keep himself from squirming away.

“Eager, are we?” Molly cooed, purposefully interpreting Caleb’s body language as encouragement rather than reflex.  Their hot breath was such a harsh contrast from the cold that Caleb was unable to tell which was which when Molly plunged their tongue deeper inside and pressed their panting nose against his clit.

Caleb whimpered, lost between the contrast of temperatures.  Every touch was overstimulating and Caleb could not keep still.  He barely even noticed his orgasm approaching until he was spasming around Molly’s tongue.  Caleb dug his heels into the mattress and raised his hips, wailing as he peaked within seconds.

No sooner had Caleb collapsed on the bed was he scrambling away from Molly and their wicked tongue.

“Stop, stop, please, stop, no more,” he begged, gasping for breath and squeezing his thighs shut.

Molly sat up and stretched alongside Caleb, settling on the bed with a satisfied sigh.  Caleb curled up with his back to Molly and his legs pulled up to his chest.  He wedged his good hand between his legs and rubbed his tender pussy, which somehow felt numb and overstimulated at the same time.

“Caleb?” Molly said, touching Caleb’s shoulder with a warm hand.  “Are you still in there, darling?” 

Caleb grunted before rolling over into Molly’s arms.  “Barely,” he answered, burying his face in Molly’s neck and smiling.  “My wrist does not hurt so much anymore.” 

“Good,” Molly said.  “Let me know if you require my services again tomorrow.” 

Caleb laughed and closed his eyes.  The last thing he noticed before falling asleep was Molly draping a heavy blanket over him and tucking him into bed, careful not to disturb Caleb’s injury.  Caleb managed to forget about his accident, lying against the curve of Molly’s warm body with the rise and fall of their chest lulling him to sleep. 


	2. Xenophilia & Hand Jobs

Caleb settled in for a quiet night of reading.  The sitting room adjacent to the tavern was empty and he found a nice armchair by the fireplace to curl up in.  Caleb turned page after page, lost in his new spellbook while the wind howled outside and Frumpkin purred in his lap. 

Everything was peaceful, for once, so Caleb should have expected it when a certain purple tiefling suddenly plopped themself down in his lap, sending Frumpkin away with an angry hiss. 

“Mollymauk,” Caleb said, flatly, turning another page. 

“Hi, Caleb,” chirped Molly, leaning back on one armrest and crossing their legs over the other. 

“Hello.  Are you….comfortable?”  Caleb furrowed his brow.  So much for a quiet night to himself. 

“Mm, very.  Thank you for asking,” Molly answered, ignoring the irritation in Caleb’s voice. 

“Can I help you, Mr. Mollymauk?” Caleb asked, shutting the book and setting it aside.  There was no use trying to concentrate if Molly was here to stay.  He shifted his legs to make room for Molly’s butt to nestle between and the tiefling stretched and yawned like a larger, heavier Frumpkin. 

“As a matter of fact, Mr. Caleb,” Molly said, dragging a single claw down the center Caleb’s chest, “You can.” 

“Let me guess.  You are either bored....”

Molly nodded. 

“...Or horny.” 

Molly nodded faster, showing their teeth as they smiled wide. 

Caleb sighed.  He turned his head away when Molly tried to kiss him, eyes darting around the room. 

“We’re alone, dear,” Molly pointed out, snuggling into Caleb’s chest.  “Everyone else has gone to bed.” 

“Oh.”  Caleb swallowed.  Molly was being cuddly and Caleb was weak, especially after the arduous journey it took to reach the tavern by nightfall.  He met Molly’s lips when they leaned up to kiss him again, allowing his initial annoyance to fade away. 

“Mm, yeah, that’s my boy,” Molly whispered against Caleb’s lips.  Their tail swayed happily off the side of the armchair as Caleb deepened the kiss.  

Caleb cupped the back of Molly’s head and dipped his tongue into their mouth.  Molly hummed in delight and reciprocated, lazily sliding their tongue against Caleb’s.  When they parted, both of them were panting. 

“You are lucky you are so hot,” Caleb murmured. 

“Would you really be so cruel as to send me away if I wasn’t?” Molly pouted. 

“There is still time,” Caleb answered, smirking playfully, “If you do not sit up and kiss me properly, I just might.” 

Molly did not need to be told twice.  They sat up and straddled Caleb’s lap, facing him, and pouted as they angled their head for a kiss. 

“Well, then, I suppose you can stay,” Caleb said, and kissed Molly again. 

They explored each other’s mouths as if they had never kissed before, nibbling on lips and sucking on tongues and spurring each other on with little noises of encouragement. 

Molly rocked forward so Caleb could feel the bulge in their trousers.   _ Gods, _ that was fast.  Caleb grabbed Molly’s ass and rolled his hips up to meet theirs, swallowing Molly’s whimpers as they grinded together. 

“What has you so worked up tonight,  _ schatz? _ ” Caleb wondered out loud, running his fingers down the base of Molly’s tail and making them shiver. 

“I can’t help myself,” Molly admitted, breathless as they squirmed in Caleb’s lap.  “It’s late, I’m sleepy, I’m alone with my  _ very attractive _ wizard...” 

“I want to see you,” Caleb interrupted, pawing at the front of Molly’s trousers.  “Can I?”

“Oh, yes,  _ please, _ ” Molly keened, sitting back on Caleb’s knees. 

Caleb undid the drawstrings that held Molly’s trousers up, reached into their smallclothes and pulled out their erect cock.  Caleb spit on his palm and wrapped his fingers around the length that was already leaking precum from its pointed tip. 

“Mmm, much better,” Molly purred, their accent thick and their voice syrupy as they lolled their head to the side and drooped their eyelids.  Watching Molly melt in his hands ignited a possessive flame in Caleb’s chest.  He squeezed harder, rubbing his thumb over the ribbed underside and watching with growing interest as the ridges expanded in response to his touch. 

“I love your cock,” Caleb whispered.  He began to gently tug on the length and could feel it twitch in his hand. 

“It’s a nice cock,” Molly agreed.  Caleb moved his hand faster, drawing little gasps and whimpers from Molly’s lips with the occasional flick of his wrist.  

Caleb normally preferred to use his mouth.  He enjoyed the unique texture of the tiefling’s dick and loved to play his tongue over the ridges, feeling them expand and fill his mouth as it grew to it’s full girth.  But this was nice, too.  He got to watch Molly’s expression change from relaxed to flustered to desperate as Caleb drew out their pleasure over the next few minutes.  He dragged his nails over Molly’s thigh, leaving goosebumps in their wake.  He tucked his fingertips on his other hand under Molly’s balls and rolled them between his fingers, feeling Molly’s dick throb as he did so. 

Precum dripped over Caleb’s fingers, making them slick and shiny.  Caleb’s fist gliding over Molly’s cock made such an obscene sound that Caleb had to hide his reddening face in Molly’s neck.  He flicked his thumb over the head, pressing on the slit and making Molly throw their head back with a guttural moan. 

“You like that, Molly?” Caleb teased, playing with a strand of the sticky substance that glistened between his fingertip and Molly’s dick. 

“Mm, fuck, Caleb,” Molly panted in reply.  “Keep doing that and I’m gonna cum.  I’m—I’m warning you, sweetheart, it’s gonna be a lot.” 

Caleb grinned against Molly’s neck and sucked a dark bruise into their purple skin.  Molly whimpered and gripped the lapels of Caleb’s coat until their knuckles went stiff. 

“Cum for me,  _ mein liebling, _ ” Caleb growled, licking the raised welt with the broad flat of his tongue.  The mere suggestion seemed to trigger Molly’s release; their balls tightened and their cock pulsed and Caleb watched in awe as Molly shot spurts of thick, translucent cum into the air that landed on Caleb’s fist and Molly’s lap.  Caleb stroked Molly through their orgasm and caught them when they collapsed, shaking, against his chest. 

They rested together for a long time, simply enjoying each other’s company.  The sounds of wind blowing snow against the window and the crackling fire reminded Caleb that there was a world outside of the one he shared with Mollymauk. 

Caleb let go of Molly’s softening cock, laughing through his nose when it flopped cutely against their thigh.  Caleb was content to bask in the afterglow until Molly grabbed his wrist, bringing his soiled hand to their lips.  Caleb’s tired eyes snapped open as Molly began licking their own cum off his palm. 

Caleb felt his smallclothes dampen instantly.  Molly drew each of Caleb’s fingers into their mouth, wrapping their tongue around the digits and sucking them clean.  A moment ago, Caleb was happy to bring Molly off and call it a night, but the sounds Molly made around his fingers had Caleb thinking twice. 

“On your knees,” Caleb ordered, watching a fiendish smirk crawl across Molly’s face.  Molly slid off Caleb’s lap and licked their lips while Caleb slouched in the armchair and spread his legs.  With his hand in Molly’s hair, Caleb was ready to take his pleasure. 

 


	3. Nipple Play & Breast Worship

**Summary for the Chapter:**

> This chapter is brought to you by: Fantasy HRT.

Molly reclined on the mattress, listening to Caleb putt around the room before bed.  They stared down at their bare chest, admiring the breasts that had recently begun to grow.  It was a slow process, but they were pleased to no longer be flat-chested.  Their breasts were barely noticeable under their shirt, but when Molly lied on their back their breasts stuck out, round and pointy.  Molly cupped a hand over each soft mound and squished them together, giggling at their own cleavage.

There was a dip in the mattress and Molly felt a heavy weight settle on their lap.  Caleb’s smiling face came into view and he leaned down to kiss Molly, tickling their abdomen with his neatly trimmed pubic hair.

“ _Guten abend,_ Mollymauk,” Caleb said, looking down at Molly’s nipples peeking out from between their fingers.  “Are you enjoying yourself?”

“Very much,” Molly purred.  They chuckled and stretched their arms above their head.  “Do you like them?”

“Hmm, I do not know yet,” Caleb said, kissing Molly’s sternum.  “I think I will need to spend more time with them to know for sure.  I hope you don’t mind waiting while I attune to them?”

“Oh, not at all,” Molly laughed, jiggling their tits from side to side.  “You can spend as much time with them as you’d like.”

Caleb hummed while he slid his hands up Molly’s slim torso and covered their breasts with both palms.  He squeezed, tentatively at first, but once he started kneading the tender flesh, Molly’s whole body flooded with warmth.

“Does this feel good?” Caleb asked, circling Molly’s nipples with his index fingers but never quite touching the buds.

“Gods, yes,” Molly groaned, shivering under Caleb’s touch.  “They’re so sensitive, sweetheart.”

“Mm, good to know,” Caleb murmured with a smirk.  He kissed Molly’s neck, gliding his lips over their tattooed skin and inhaling their intoxicating scent.  He left a trail of wet kisses down the center of Molly’s chest, still exploring their breasts with curious fingers.  With his head between them, Caleb smushed Molly’s tits together, trapping his face between them.

Molly smiled wide and showed their appreciation by stroking Caleb’s hair.  They laughed at the part of themself that had worried Caleb would not find their larger tits attractive.  Caleb was obviously enjoying himself as he nuzzled deeper into the valley of their breasts, evident by the desire dripping from Caleb’s pussy, pooling in the divots of Molly’s hips and running down their sides.

Molly breathed heavily through parted lips as their nerves lit up under Caleb’s roaming hands.  They swore they could feel the wizard’s magical energy sparking under their skin.  Caleb’s thumb flicked over their nipple, followed by a burst of pleasure that struck Molly’s core.  Molly gasped and arched their back while Caleb raised his head, red faced and giggling.

“Keep doing that,” Molly pleaded, gripping the headboard and holding on tight.

“What, this?” Caleb teased, flicking their nipple again and making Molly whine and buck their hips.  “Gods, you really _are_ sensitive.”

Where Caleb’s hands went, his lips followed.  He began kissing around one breast and working his way towards the center, suckling the skin between his teeth and leaving red marks in their wake.  Molly cried out when Caleb circled their nipple with the tip of his tongue, sending another powerful jolt straight to Molly’s cock.

“Oh, Caleb, darling,” Molly whimpered raising their hips.  Their cock throbbed neglected behind Caleb.  “Touch me, please?”

Caleb shook his head.  “Do you think you can come from this?”  He rolled a nipple between his fingers, making Molly squirm.

“I—I don’t know,” Molly admitted, “I’ve never tried.”

“Do you want to try?”

“Oh, fuck, _yes,_ “ Molly hissed, smacking their tail on the bed.

While Molly whimpered, Caleb slipped into silence when he took one impressively erect nipple between his lips and sucked.  Molly arched their back and trembled as the hot coils of arousal tightened in their core.  Caleb had to hold Molly down with one hand on their stomach to keep them from thrashing while he licked and sucked and drove Molly wild.  

“Caleb, Caleb— _haahh!_ ” Molly screamed when Caleb bit their nipple.  He tugged it between his teeth before letting it slide past his lips.  Molly’s hand flew to the back of Caleb’s head, gripping his hair and forcing him down until he latched onto Molly’s other nipple.  He rolled the bud between his teeth just enough to hurt while rubbing circles over the stiff, wet nub on the other side.

The need for release was growing rapidly in Molly’s abdomen.  They felt they might cum at any moment, so it was as if Caleb knew that Molly was on the edge when he began to kiss their lips instead.  He sucked on Molly’s tongue, grazing his teeth over the pronged tip and flicking it with his own.

“You will cum for me,” Caleb said when he pulled back, staring into Molly’s wild eyes with his gorgeous blues, darkened by lust.

“I will cum for you,” Molly repeated, panting softly.  “I’m so close, Caleb, please, hurry...”

Caleb nuzzled Molly’s breasts before returning his attention to their nipples.  He drew Molly’s orgasm closer to the surface with every suck, nibble and pinch, accompanied by his ragged breathing that felt hot against Molly’s skin.  Molly wondered where the in the nine hells Caleb learned how to do it, but every time he tried to speak, Caleb would do _something_ with his mouth that made Molly’s brain flatline.

With one more hard, long suck, it was over.  Molly bucked so hard that they almost threw Caleb off them when they came, completely dry.  They squeezed their eyes so tight that they saw dancing lights behind their eyelids while their whole body went taut.  They trembled from the aftershocks and held Caleb against their body, smushing their tits against his chest. 

“ _Mein gott,_ ” whispered Caleb, gazing adoringly at Molly’s flushed face.  The dark plum blush went all the way down to their breasts.  “That was—oh, _scheisse_ , Mollymauk, that was so hot.”

Molly blinked until Caleb’s wide-eyed expression came into focus.  They pulled him down for a kiss but quickly ran out of air, their chest still heaving and their cock still aching. 

“So what’s the verdict, Mr. Caleb?” Molly asked, smiling against his partner’s lips.

“Mm, I love them,” Caleb said, dancing his fingers over one soft mound before Molly sucked in a breath and gently took his hand away.  They entwined their fingers and Molly kissed each of their knuckles, overjoyed that Caleb loved their tits as much as they did.

“Wait a minute, love,” Molly said.  “Please, they’re too tender.”

Caleb laughed and nibbled Molly’s jaw.  “Okay,” he said, flopping onto his back beside Molly.  “It’s my turn, now.”

Molly grinned, showing their teeth.  They rolled on top of Caleb, their erection still prominent between their legs.  “Get comfortable, darling,” Molly said, their hands creeping up Caleb’s torso.  “I want to take my time with you.”

 


	4. Semi-pubic & Formalwear

**Summary for the Chapter:**

> Takes place during episode 33.

When Caleb stepped out from the alleyway, Molly knew they were  _ fucked _ . 

Caleb’s outfit was spotless.  His coat had transformed from tattered wool to casually worn leather.  Molly wanted to tear the crisp white cravat from Caleb’s throat with their teeth.  They wanted to send those brass buttons flying when they tore open that navy blue vest.  They wanted to yank down those tight brown trousers and see what kind of smallclothes were hidden inside.  Molly’s cock twitched when they noticed the black leather boots that came up to Caleb’s knees. 

_ Gods above, I want him to step on me, _ Molly thought.  Molly was so distracted by what they wanted to do to Caleb that they did not realize they had been walking forward until they were face to face with the man himself. 

“Mollymauk,” Caleb greeted, allowing Molly to step into his space. 

“Good evening, handsome,” Molly purred, leaning in to kiss Caleb’s cheek. 

Caleb blushed.  Of course he did—all Molly had to do was smile at him a certain way to make the human’s cheeks turn pink.  “Are you ready for the performance?” Caleb asked, nervously.  The outfit would certainly draw more attention to Caleb than he was used to, as demonstrated by one purple tiefling caressing his jaw.  It was strange, Molly thought—Caleb looked freshly shaven, but Molly could feel the course texture of hair under the disguise. 

“Not quite,” Molly answered, pretending to adjust Caleb’s perfectly symmetrical lapels as an excuse to touch him.  They leaned in close and whispered into Caleb’s ear, “There’s something I have to take care of first.” 

Caleb’s face grew even redder.  “We—we do not have time for this, Molly.” 

“Nonsense,” Molly replied.  They flattened their palms against Caleb’s chest and began backing him towards the alley from which he came.  “It doesn’t start for half an hour.  I’ll be done with you in fifteen minutes.” 

As soon as Caleb’s back hit the wall, his arms flew around Molly’s neck as Molly kissed him, forceful and hungry.  Molly groaned happily when Caleb kissed back, equally passionate with tongue and teeth. 

“We should not be doing this,” Caleb gasped when Molly began kissing the side of his neck. 

Molly eased back.  “Do you want to stop?”

“Fuck, no,” growled Caleb.  He grabbed Molly’s hips and pressed their body flush against his own.  Molly knew Caleb could feel their erection by the wide-eyed look of recognition on his face. 

“This is what you do to me,” whispered Molly, rolling their hips and rubbing themself against Caleb’s belly.  “You in this outfit, and those fucking boots.” 

“Oh, you like my boots?” Caleb asked, smirking.  He canted his hips to meet Molly’s as they pressed Caleb against the wall. 

“Gods, yes,” hissed Molly, “Almost as much as I would like to fuck you.” 

Caleb pushed Molly’s hips away.  For a moment Molly was worried that they had gone too far until Caleb started hastily undoing their trousers.  Molly whined when Caleb pulled out their fully erect cock. “How do you want me?” Caleb asked, staring Molly down as he gave their cock a few rough strokes. 

Molly responded by spinning Caleb around and pinning him, face first, to the rough stone.  “Quick and dirty,” Molly spoke low in Caleb’s ear.  They made quick work of Caleb’s trousers and yanked them down to his knees.  

Caleb spread his legs as far as his trousers would allow before Molly could even tell him to.  Molly’s hand darted between Caleb’s legs and they dragged two fingers through his slick desire, making Caleb shiver from more than the cool night air.  Caleb sucked in a sharp breath when Molly slipped their fingers inside his wet pussy without warning.  He pushed back against Molly’s hand while they finger-fucked him, stretching him open in preparation for Molly’s cock. 

Molly suddenly heard voices in the distance; their friends were talking around the corner where they were gathered in front of the building.  Someone would come looking for them soon, and while Molly could not care less about who saw their dick, they knew Caleb would likely implode from embarrassment. 

“Molly,  _ hurry, _ ” Caleb hissed, lifting his ass in the air. 

Molly pressed the head of their cock to Caleb’s entrance and pushed inside.  They signed loudly as they pressed further into Caleb’s tight heat. 

“Fuck, Caleb, you feel wonderful,” Molly groaned, panting hotly into his ear.  They continued to whisper praises as they reached around Caleb’s front and began rubbing his clit.  They grabbed his hips with their free hand and fucked Caleb deeply, gradually picking up the pace.  Caleb bucked backwards and failed to muffle the whimpers that rose in the back of his throat whenever the tip of Molly’s cock hit the spot inside him that made his knees weak. 

The wet sound of Molly’s cock sliding in and out of Caleb’s dripping cunt made Molly’s balls tighten, warning them of their impending orgasm.  They called out to Caleb, “Fuck, I’m gonna cum! Where do you want it?”

“Don’t you dare cum inside me,” Caleb warned, pushing Molly off him with an elbow to their ribs.  “Do not soil my clothes.” 

“I won’t,” Molly promised.  They pulled out and aimed their cock at the space between Caleb’s legs.  They came with a shout muffled by the scruff of Caleb’s neck while thick spurts of cum splattered the stone wall. 

“Molly!” Caleb snarled, turning around and glaring at the tiefling.  He bumped Molly’s foot with his own.  Molly looked down to see the smear of cum across the top of Caleb’s boot. 

“Caleb, I’m—” Molly began, but they had no time to apologize before Caleb was pushing Molly’s shoulders down.  Their cheeks burned with shame as they kneeled obediently at Caleb’s feet, their softening cock still hanging out the front of their trousers. 

“You will pay for that later,” Caleb said, threading his fingers through Molly’s hair and pulling their head towards his cunt.  “But for now, you will finish me.” 

“Of course, Caleb,” Molly said, their heart beating faster with the promise of  _ later. _  They spread Caleb open with their thumbs and began licking between his lips with slow, tender strokes of their tongue.  They took their time exploring and teasing Caleb’s clit until the voices in the distance grew louder. 

“ _ Hurry, _ ” Caleb hissed, pressing Molly’s mouth flush against his clit with a hand on the back of their head.  The feeling of being used made Molly’s cock stir again, but turned their focus on Caleb. They reached around and grabbed Caleb’s ass, closed their lips around his clit and sucked.  They could feel Caleb’s muscles tremble, letting them know that he was close. 

“ _ Scheisse, _ Molly, Mollymauk, fuck,” Caleb muttered under his breath, pulling Molly’s hair so hard that their scalp began to ache. 

Molly flicked their tongue hard against Caleb’s clit, once, twice, and Caleb was cumming hard.  Caleb dropped both hands to Molly’s shoulders for support and Molly pressed Caleb’s hips against the wall to keep him upright as he rode out his orgasm in silence. 

“Mm, fuck, yeah,” Molly purred, pulling up Caleb’s trousers and then standing up.  They began straightening Caleb’s coat and tucking his cravat back into the vest before whispering against their lips, “Good boy.”

Caleb was too breathless to speak, but he replied by crushing their mouths together and licking his cum from Molly’s lips. 

“Wasn’t kidding,” he said, finally, giving Molly’s balls a squeeze before tucking their cock back into their trousers.  “You will pay for cumming on my boot.” 

Molly did not even try to keep a gleeful smile from blooming across their face.  Once they were both presentable, they emerged from the alley, arm in arm. 

“I’m looking forward to it,” Molly said before waving hello to their friends. 


	5. Boot Worship

**Summary for the Chapter:**

> Continued from last chapter.

_ You will pay for that later, _ Caleb’s voice echoed in Molly’s head as they knelt on the floor of their room in the Lavish Chateau while Caleb paced around them in slow circles.  Molly kept their head down but they could hear the rhythmic  _ thunk, thunk, thunk _ of Caleb’s boots on the hardwood floor while their heartbeat accelerated with each footstep.  Eventually, Caleb took a seat in the chair that had been placed in the center of the room, facing Molly. 

Caleb’s boots, after the disguise spell had ended, were worn and dusty, with mud on the soles and who knew what else flaking off the sides. 

“Caleb,” Molly started, looking up at the human.  They knew the answer before they asked, “How many times have you washed these boots?” 

Caleb cocked an eyebrow.  “After this time? It will have been once.”  He crossed his legs and pointed his toe at Mollymauk, rotating his ankle to display the full scope of the boot. 

Caleb’s tone sent chills down Molly’s spine.  He could have easily cast a prestidigitation spell and made his boots look as good as new.  But this was Molly’s punishment, they surmised—the evidence on Caleb’s smirking visage as he bounced his foot impatiently.  At the same time, it felt like an honor to be the only one who will have had the chance to clean the boots of the man they adored. 

Molly’s cock bobbed between their legs but they ignored it; they had been forbidden from touching themself, an instruction that they would not disobey. 

“You may begin, Mollymauk,” Caleb said, his voice gentle but commanding. 

Molly nodded and held the heel of Caleb’s boot in their palm.  They picked up a horsehair brush from the array of tools around them and began to sweep the debris from the surface of one boot and then the other.  An impressive pile of dust accumulated on the floor, proof that Molly had done a thorough job.  They looked up at Caleb for approval. 

Caleb hummed appreciatively and smiled warmly.  “You are doing well, Mollymauk, but you are not done yet.” 

Molly nodded and got back to work.  They began to dab the leather with a rag dipped in vinegar, careful not to moisten the material too much.  They scrubbed a dry rag over the toe and behind the heel to remove the last of the grime, working until Caleb’s boots were virtually spotless.  They would never look as new or shiny as the ones Caleb conjured for his disguise, but Molly was proud of their work.  When others would comment on the wizard’s atypical cleanliness, Molly would be satisfied knowing that  _ they _ were responsible. 

Molly’s dick was so hard by the time they finished cleaning that it was difficult to ignore.  They subconsciously rolled their hips, seeking contact with nothing, but not without alerting Caleb’s attention to their growing problem. 

“Oh, Molly,” Caleb cooed, “Are you uncomfortable,  _ schatz?” _  He cupped Molly’s cheek and tugged their lower lip down, retracting their thumb before Molly’s tongue darted out to lick it.  Caleb leaned back with both hands on the armrests.  “Dry them off, please.  I do not want the leather to rot.”

Molly nodded and patted the leather dry, instantly falling into a trance.  They rubbed the towel over the toe again and again just so they could keep touching Caleb’s boot.  They were so focused that nothing else in the room mattered as much as the task before them.  They barely felt a hand in their hair until Caleb tugged, forcing Molly to look at him. 

“Hey, are you in there?” Caleb asked, tenderly, threading his fingers through Molly’s curls. 

“Y-yeah.  I’m right here.”  Molly blushed and nodded, setting the rag aside. 

“Look at how nice my boots look,” Caleb said, holding one foot up and then the other.  “Thank you, Mollymauk.  You did a great job.” 

Molly sat up taller, bringing their shoulder blades together and basking in Caleb’s praise.  They leaned their head back to let Caleb stroke their cheeks and jaw and neck, so they were not expecting to have the sole of a boot to pressing against their cock. 

“Ah, you are hard from this?  From cleaning my boots?” Caleb teased, toeing Molly’s dick. 

“I just want to please you, Caleb,” Molly said, cheeks burning.  “Is there anything else I can do for you, sweetheart?”

“ _ Ja, _ there is,” Caleb purred, spreading his legs apart, one foot on the ground and one pinning Molly’s cock to their stomach.  “We were in such a hurry when you made me cum, it was barely satisfying.  Come here, _ mein liebling, _ and finish the job.” 

Molly braced themself with their hands on Caleb’s knees and pressed their mouth and nose into the fabric, inhaling deeply and shuddering on the exhale.  They felt lightheaded as Caleb’s musky scent, mixed with sweat and cum, saturated their brain and dragged them to a place where their thoughts could not reach them. 

Molly mouthed Caleb’s crotch through his trousers, making a wet patch form between his legs.  They nuzzled Caleb’s thighs and traced their tongue around Caleb’s pussy until Caleb pushed their head away and quickly unbuttoned his trousers, letting them fall and pool around his ankles.  Molly was delighted to see the wet patch on Caleb’s smallclothes was so dark that it could not have been dampened only by Molly’s saliva. 

“Let me see you,” Molly begged.  “I wanna see your handsome pussy up close.” 

Molly watched with wide eyes as Caleb lifted his hips and shimmied down his smallclothes, revealing his dripping pussy and two inch long clit.  Molly laughed, puffing hot air over Caleb’s cunt.  “You’re hard from this, too, darling,” Molly teased, dragging one finger up Caleb’s slit and examining the glistening cum running down their knuckles. 

“Of course I am!” Caleb snapped, blushing deeply.  “You— _ you— _ ”  Caleb grabbed the back of Molly’s head and smushed their face into his crotch.  Molly shut up instantly; the only sounds they made were groans and whimpers in the back of their throat as they wedged their nose between Caleb’s lips. 

Molly started by licking up and down Caleb’s slit, bumping their nose against his heavy clit with every pass and nod.  Caleb gasped when Molly finally pushed their tongue inside, dextrously teasing him with every twist of their tongue.  Caleb whined when Molly suddenly pulled away, trying to clench around the muscle to keep it in place.  Caleb was about to complain before Molly began to trace their fingers along the slit, using their first two fingers to part the labia and and peek inside. 

“Absolutely gorgeous,” Molly whispered, kissing above Caleb’s clit and teasing a finger inside.  Caleb clenched around the digits and Molly quickly added a second, then a third into Caleb’s cunt.  Molly’s fingers grew slick with Caleb’s desire until it was no effort at all to thrust them in and out, drawing deep, needy moans from Caleb’s lips.  Molly could tell by his quickened breathing and the amount of precum running down their wrist that Caleb was close. 

“Mmm, so easy,” Molly purred, curling their fingers upwards, searching for Caleb’s g-spot.  Caleb’s thighs trembled as Molly thrust their fingers deeper.  Pride swelled in Molly’s chest when Caleb’s body went taught and the grip on Molly’s hair tightend almost painfully.  They sealed their mouth over Caleb’s pussy when he came, squirting his release down Molly’s throat. 

“Do you forgive me?” Molly asked when Caleb stopped trembling.  They grinned up at him, licking the rest of Caleb’s cum from around their mouth. 

“Ja,” Caleb replied.  “You are forgiven for you crimes against my boots.”  He leaned down and took Molly’s face between shaking hands, stroking their flushed cheeks with his thumbs.  “I hope you are ready for your reward. On the bed, please.” 

Molly’s eyes lit up and he nodded eagerly, scrambling to the bed as instructed. 

“Oh, Molly,” Caleb sighed, stepping around the sizeable puddle of precum that had dripped onto the floor betwen Molly’s legs.  “When will you learn to stop making messes?”

Molly wrapped his arms around Caleb when he climbed on top of them, giggling when Caleb began smothering them with kisses. 

“When you stop rewarding me for making them,” Molly answered, grinning wildly. 


	6. Watersports

**Summary for the Chapter:**

> It's pee. This chapter is unrelated to the rest, so feel free to skip it if it's not your thing.

Caleb had barely undone his belt before he heard a familiar voice call to him through the trees.

“Caleb?  Is that you?” Molly shouted over the rush of water.  Caleb had snuck away from the main camp to pee and he had assumed Molly had done the same, but when Caleb followed their voice to the riverbank, he saw Molly standing in shallow water. 

“Hi, Molly,” Caleb greeted, nearly tripping over Molly’s neatly folded clothes on the shore. 

“Hello!”  Molly waved and slapped the water with their tail.  “Have you come to join me?” 

“I have to take a piss,” Caleb replied, looking towards the trees, “Which I have not done yet, so, ah….excuse me.” 

Molly pouted.  “What’s the rush, darling?  Come out here.  I need someone to wash my back.” 

Caleb sighed and began to undress.  He was weak for the tiefling and it was a problem, especially when the sound of water made the need to pee even worse.  He tried not to squeeze his thighs together too conspicuously as he waded into the river and into Molly’s embrace.  He snorted when he felt Molly’s dick bump into his thigh. 

“Hmm, wash your back?  You are not fooling anyone, Mollymauk,” Caleb said, giggling when Molly squeezed his ass. 

“I never intended to deceive you, my brilliant wizard,” Molly cooed, tilting their head to kiss him.  Molly’s lips were wet and cold from the water but their tongue was hot when it wormed its way past Caleb’s lips.  

Caleb melted into the kiss, ignoring his bladder’s demands.  It was so easy to get lost in Molly’s charm that Caleb almost forgot the reason why he was there.  Their hands mapped out each other’s skin while the water lapped at their thighs. 

“I miss being alone with you,” Molly complained, leaving a trail of wet kisses down Caleb’s throat. 

Caleb tipped his head back.  “Mmm, I can tell,” he said, rubbing his cunt against Molly’s erection.  “Will you let me piss if I promise to let you fuck me?” 

“Does it have to be in that order?”  Molly asked, making Caleb choke on his own spit.  He felt a jolt of pleasure when the urge to pee came rushing back to him and shivered in response.  He feared he might wet himself when Molly backed him up against a rock and hauled him up on top of it, but he was relieved by the pressure of cold stone between his legs. 

Caleb groaned in defeat and pulled Molly to him, finally welcoming them into his space.  He cupped their cheek and ran his fingers over the curve of their hip.  “Don’t complain if I piss on you, then,” he warned, wrapping his legs around Molly’s waist. 

Molly laughed into Caleb’s ear.  “That won’t be a problem, sweetheart.”

Molly’s fingers danced between Caleb’s legs, tickling the creases between his thighs and stroking his soft lips before parting them and admiring the flushed pink skin inside.  Caleb was already wet with desire when Molly slipped a finger into his cunt, then another, and another.  Gods, it really had been a long time since he had been touched; Caleb was starved for it.  He wrapped his arms around Molly’s neck and took his pleasure, remembering just how talented Molly was with their fingers.  His heavy breathing hitched when Molly curled their digits into the spongy tissue behind Caleb’s urethra. 

“Don’t—” Caleb pleaded, clenching his muscles around Molly’s fingers, but it was too late.  He could tell by Molly’s sly smile that something besides Caleb’s slick had dribbled onto their hand. 

“What’s this?”  Molly purred, raising their hand to their mouth and licking their palm.  They made a sour face, then grinned at Caleb and purred, “Oh, sweetheart, you really are desperate.” 

“Molly!” Caleb hissed, cheeks burning with shame.  He rocked against the uncomfortable surface of the boulder, trembling with the effort it took to stem the flow. 

“Shh, it’s okay,” Molly assured him, placing Caleb’s hand around their fully hard cock.  “See? So am I.” 

“Gods, you are so weird,” Caleb huffed.  Fed up with Molly’s teasing, he scooted forward and pressed the head of Molly’s dick between his pussy lips.  He stared Molly down in the few seconds it took him to convince his sore abdominal muscles to let go, watching Molly’s eyes grow wide and their mouth fall open as Caleb’s hot piss trickled down their cock. 

“And you are a wonderful enabler,” Molly said, jerking off under the stream.  Caleb was reluctant to admit it but fuck, it was  _ hot.   _ Molly rarely said  _ no _ to anything, but Caleb thought this would at least cause some hesitation. 

“Put it in me,” ordered Caleb, suddenly overwhelmed with the need to to be filled even more than he already was.  “ _ Hurry. _ ”

Molly did as they were told.  They pushed inside with a groan, helped along by Caleb’s heels pressing into their lower back.  Caleb sighed in relief when Molly’s length stopped the flow but the urgency persisted in his heavy bladder. 

When Molly began to move, Caleb fell onto his back and arched up off the stone, digging his fingers into the gritty surface.  The fact that they were naked in the woods with their friends nearby was forgotten by Caleb as the only things keeping him from wetting himself were his own concentration and Molly’s cock pressing on his urethra. 

He imagined that he could feel the liquid sloshing around inside with every thrust of Molly’s hips.  That mental image coupled with the sharp pangs of pleasure he felt every time the tip of Molly’s cock hit deep inside his cunt brought Caleb closer to the edge. 

“How are you doing, love?” Molly asked, flushed and panting above him. 

“Close,” Caleb choked out, barely able to breathe.  He was either going to piss or cum, and at this point he did not care which happened first as long as it would bring him some relief. 

“Fuck, me too,” Moly groaned.  They dropped their head to Caleb’s shoulder and froze.  Caleb felt their cock pulsing as Molly came inside of him, and that was when Caleb lost it.  The force of his release pushed Molly’s cock out, followed by a powerful stream of pee that sprayed their dick and thighs. 

“Caleb, fuck, yeah, that’s my good boy,” Molly murmured, holding their cock under the flow.  Caleb whimpered as his entire lower body spasmed, his muscles finally releasing the stress of holding it for so long. 

When the last of his bladder’s contents trickled to a stop, Caleb pushed himself to his elbows and met Molky’s eyes.  He saw no judgment on their face, just love and adoration and post-orgasmic bliss.  Caleb smiled sweetly and let Molly help him sit up. 

“Well,” Molly said, grinning so wide their eyes narrowed, “That’s one way to get clean.” 

Caleb scowled.  Gods, to think he had almost kissed them.  Instead, he put his foot in the middle of Molly’s chest and shoved them backwards into the river. 

 


	7. Distractions & Edging

**Notes for the Chapter:**

> It's looking like this might be the last or second-to-last chapter. I will not have time to write all 12 chapters (in October, anyway), but I am happy to have gotten this far.

“You,” Caleb hissed, sitting beside Molly with his back against the headboard, “Are being quite the distraction.”

“You need a distraction, sweetheart,” Molly said, smiling at Caleb who had finally decided to pay attention to them.  They were stretched out on the bed, completely nude. “You’ve been working too hard.” 

“I work hard so that we can have things that we need.  Like heat and light and food.” 

“I have needs, too,” argued Molly, “And if my husband won’t fulfill them, who will?”

“Ah, you want me to touch you?” Caleb quirked an eyebrow, glancing down where Molly’s hard dick rested against their belly.  He took Molly’s cock in his hand and it and gave it a few rough tugs.  Molly whined, partly in discomfort but mostly in delight.  “You have not cum yet.  Why is that?”

“Mm, I like waiting,” Molly answered, wiggling their hips.  “It’s better when I don’t cum right away.” 

“I see,” Caleb said, as if he did not already know that about Molly.  He gave their cock a firm squeeze before letting go.  He returned his attention to the laptop on his knees.  “Then you can wait patiently until I am done,  _ ja _ ?” 

Molly stared at Caleb with pleading eyes.  “You’re just staring at that screen! Have you written anything in the past half hour?”

“I have had a person masturbating loudly in my bed all evening.  Pardon me for being a bit unfocused.” 

“ _ Caaaleb _ ,” Molly whined, reaching for their husband.  Caleb knocked their hands away. 

“None of that,” he snapped.  Caleb began typing again, making faces at his computer while cutting and pasting and rearranging paragraphs.  His heart was no longer in his work, but he had to have  _ something _ by tomorrow. 

When Molly had given up hope trying to get Caleb’s undivided attention, they sighed and closed their eyes.  Their cock softened a little from neglect, and Molly suspected it would be a long time until they got to cum. 

A few minutes later, however, Caleb reached over and wrapped his hand around Molly’s cock.  He kept his eyes on the screen and typed slowly with one hand while the other smeared precum over the length and stroked it until it was hard again.  He let go as soon as Molly’s breath sped up. 

“Keep touching yourself,” Caleb demanded.  “I want you nice and hard for me when I am done.  Stop when you are close, okay? You will not cum until I say so.” 

Molly did what Caleb instructed and teased the sides just under the head with their fingers.  Their balls felt heavy with the need for release, but they knew Caleb was watching out of the corner of his eye. 

“Stop,” Caleb said, and Molly did.  Caleb turned his head and smiled at them.  “Ah, that was very good.  Shall I give you a little taste of your reward?” 

Molly nodded eagerly, watching Caleb put the laptop down and crawl over to them on his knees.  Caleb lowered his head and Molly’s eyes rolled back when he took Molly’s entire length into his mouth at once.  But after a few powerful sucks, Caleb pulled away.  He wiped his mouth, still smiling sweetly, then he returned to his computer without a word. 

“Oh, fuck,  _ Caleb, _ ” Molly hissed.  They shivered; the air felt cold against their dick and Molly swore that ten more seconds inside Caleb’s warm, wet mouth would have had them cumming hard. 

Molly did not know how long it was before Caleb closed his laptop and set it on the bedside table.  Their heart swelled with hope when he lied down on his side and faced them.  “You have been very good, Mollymauk,” Caleb said, petting their thigh.  He saw how dark and swollen their cock looked.  “Ah, poor thing.  Let me help,  _ liebling. _ ” 

Molly whimpered and lifted their hips when Caleb twisted his fist around their aching length.  He began pumping them slow, then increasing the pace until Molly was panting and clenching their thighs.  “Close, Caleb, I-I’m so close,” they warned, but before that could happen, Caleb took his hand away. 

“Oh, gods, Caleb, please, please finish me, I’ve been waiting so long, I’ve been so good—”

With Caleb’s fist around the base of Molly’s cock, Caleb took the head between his lips and swirled his tongue around the pointed tip.  He teased the slit and bobbed his head up and down a few times, making Molly howl and tear the sheets with their claws. 

“Cumming!” Molly shouted, squeezing their eyes shut and arching off the bed.  Caleb pulled back instantly, but Molly was already there.  Their cock pulsed as their orgasm hit, crashing over them in waves of pleasure.  But something was wrong.  When their orgasm ended, they felt just as frustrated as before. Molly had cum completely dry. When they opened their eyes, Caleb’s smile looked almost sadistic. 

“Oh,  _ mein schatz, _ what happened?” Caleb cooed, his voice dripping with twisted satisfaction. 

“You fucker,” Molly groaned.  “You ruined it—fuck!” 

“Mm, _ ja, _ like like you ruined my concentration,” Caleb said, rolling onto his back and closing his eyes.  “Tomorrow is a new day, Mollymauk.  Perhaps you will learn behave yourself from now on.” 


End file.
